(4R*,4aS*,4bS*,5R*,10aR*)-4-Hy-droxy-4a,5-dimethyl-2-(propan-2-yl)-1,4,4a,4b,5,6,7,8,10,10a-deca-hydro-phenan-thren-1-one.

In the title compound, C(19)H(28)O(2), the A ring adopts a chair conformation. Both the B and C rings adopt envelope conformations with the C atoms common to both rings and adjacent to the carbonyl and hydroxyl groups, respectively, lying 0.604 (3) and 0.634 (3) Å out of the mean planes defined by the remaining five C atoms of rings B and C, respectively (r.m.s. deviations = 0.0100 and 0.0157 Å, respectively). The formation of linear supra-molecular C(7) chains along the a axis mediated by hy-droxy-O-H⋯O(carbon-yl) hydrogen bonds is the most prominent feature of the crystal packing.

Related literature

For background to the biological activity of some diterpene compounds, see: Guo et al. (2011 ▶); Slusarczyk et al. (2011 ▶). For the synthesis, see: Ferreira (2002 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H28O2

M = 288.41

Orthorhombic,

a = 6.5507 (9) Å

b = 11.733 (1) Å

c = 22.338 (3) Å

V = 1716.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 290 K

0.15 × 0.12 × 0.09 mm

Data collection

Enraf–Nonius CAD-4 Mach 3 diffractometer

2272 measured reflections

1945 independent reflections

1077 reflections with I > 2σ(I)

R int = 0.038

3 standard reflections every 30 min intensity decay: 2.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.122

S = 1.02

1945 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.11 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and MarvinSketch (Chemaxon, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048008/hb6477sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048008/hb6477Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H28O2	F(000) = 632
Mr = 288.41	Dx = 1.116 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 23 reflections
a = 6.5507 (9) Å	θ = 9.1–16.5°
b = 11.733 (1) Å	µ = 0.07 mm−1
c = 22.338 (3) Å	T = 290 K
V = 1716.9 (4) Å3	Irregular, colourless
Z = 4	0.15 × 0.12 × 0.09 mm

Enraf–Nonius CAD-4 Mach 3 diffractometer	Rint = 0.038
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.0°
graphite	h = −1→8
ω/–2θ scans	k = −14→0
2272 measured reflections	l = −27→0
1945 independent reflections	3 standard reflections every 30 min
1077 reflections with I > 2σ(I)	intensity decay: 2.0%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.0441P] where P = (Fo2 + 2Fc2)/3
1945 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.11 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.5700 (5)	0.1474 (3)	0.87731 (12)	0.0536 (8)
H1	0.6626	0.1974	0.8996	0.064*
C2	0.6209 (4)	0.1683 (2)	0.80946 (13)	0.0488 (8)
C3	0.4355 (4)	0.1501 (3)	0.76804 (12)	0.0478 (7)
H3	0.3371	0.2113	0.7758	0.057*
C4	0.4904 (5)	0.1535 (3)	0.70352 (13)	0.0527 (8)
H4	0.3867	0.1723	0.6769	0.063*
C5	0.6731 (5)	0.1322 (3)	0.68010 (13)	0.0508 (7)
C6	0.8399 (5)	0.1005 (3)	0.72195 (15)	0.0559 (8)
C7	0.7936 (4)	0.0895 (2)	0.78799 (14)	0.0526 (8)
H7	0.9173	0.1121	0.8096	0.063*
C8	0.7588 (5)	−0.0363 (3)	0.80105 (14)	0.0616 (9)
H8A	0.6508	−0.0653	0.7755	0.074*
H8B	0.8823	−0.0789	0.7925	0.074*
C9	0.7016 (6)	−0.0514 (3)	0.86456 (15)	0.0656 (9)
H9	0.7258	−0.1223	0.8818	0.079*
C10	0.6191 (5)	0.0279 (3)	0.89854 (14)	0.0592 (8)
C11	0.5787 (7)	0.0058 (4)	0.96343 (16)	0.0875 (13)
H11A	0.6721	0.0509	0.9874	0.105*
H11B	0.6046	−0.0739	0.9720	0.105*
C12	0.3627 (8)	0.0344 (4)	0.98085 (18)	0.1012 (15)
H12A	0.2688	−0.0165	0.9606	0.121*
H12B	0.3454	0.0245	1.0237	0.121*
C13	0.3167 (8)	0.1551 (3)	0.96402 (16)	0.0900 (12)
H13A	0.4014	0.2053	0.9880	0.108*
H13B	0.1753	0.1712	0.9738	0.108*
C14	0.3521 (6)	0.1821 (3)	0.89755 (16)	0.0699 (10)
H14	0.2546	0.1368	0.8743	0.084*
C15	0.6977 (6)	0.2914 (3)	0.80117 (15)	0.0750 (11)
H15A	0.5933	0.3438	0.8135	0.113*
H15B	0.7300	0.3041	0.7598	0.113*
H15C	0.8177	0.3030	0.8251	0.113*
C16	0.7253 (5)	0.1371 (3)	0.61470 (13)	0.0627 (9)
H16	0.8109	0.0708	0.6056	0.075*
C17	0.8497 (8)	0.2431 (4)	0.60174 (17)	0.1106 (16)
H17A	0.8863	0.2445	0.5601	0.166*
H17B	0.9713	0.2425	0.6257	0.166*
H17C	0.7704	0.3095	0.6111	0.166*
C18	0.5396 (6)	0.1315 (4)	0.57472 (15)	0.0879 (13)
H18A	0.5818	0.1327	0.5336	0.132*
H18B	0.4530	0.1958	0.5826	0.132*
H18C	0.4659	0.0624	0.5826	0.132*
C19	0.2980 (9)	0.3082 (3)	0.88848 (17)	0.1022 (16)
H19A	0.1605	0.3215	0.9015	0.153*
H19B	0.3100	0.3272	0.8468	0.153*
H19C	0.3898	0.3547	0.9114	0.153*
O1	1.0090 (3)	0.0749 (2)	0.70292 (10)	0.0824 (8)
O2	0.3390 (3)	0.04403 (17)	0.78121 (9)	0.0563 (6)
H2o	0.2390	0.0359	0.7595	0.085*

	U11	U22	U33	U12	U13	U23
C1	0.0577 (17)	0.0556 (18)	0.0474 (17)	−0.0035 (17)	−0.0097 (15)	−0.0039 (15)
C2	0.0480 (18)	0.0450 (17)	0.0533 (17)	−0.0047 (15)	−0.0104 (15)	0.0007 (13)
C3	0.0434 (16)	0.0470 (17)	0.0529 (17)	0.0061 (15)	−0.0055 (13)	0.0023 (14)
C4	0.0456 (16)	0.0577 (19)	0.0546 (18)	0.0020 (16)	−0.0140 (15)	0.0068 (15)
C5	0.0432 (16)	0.0584 (19)	0.0509 (16)	−0.0044 (16)	−0.0060 (15)	0.0036 (15)
C6	0.0357 (15)	0.068 (2)	0.064 (2)	−0.0068 (16)	−0.0025 (16)	0.0015 (16)
C7	0.0381 (16)	0.0631 (19)	0.0566 (19)	−0.0061 (15)	−0.0127 (15)	0.0056 (16)
C8	0.0565 (18)	0.060 (2)	0.068 (2)	0.0132 (17)	−0.0010 (17)	0.0056 (17)
C9	0.069 (2)	0.057 (2)	0.071 (2)	0.0115 (19)	−0.0020 (18)	0.0172 (17)
C10	0.0614 (19)	0.062 (2)	0.0543 (19)	0.0002 (18)	−0.0080 (17)	0.0110 (17)
C11	0.112 (3)	0.089 (3)	0.062 (2)	−0.001 (3)	0.001 (2)	0.012 (2)
C12	0.127 (4)	0.109 (3)	0.068 (2)	−0.018 (3)	0.028 (3)	0.005 (2)
C13	0.094 (3)	0.108 (3)	0.068 (2)	0.009 (3)	0.014 (2)	−0.017 (2)
C14	0.072 (2)	0.074 (2)	0.064 (2)	0.007 (2)	0.002 (2)	−0.0152 (17)
C15	0.092 (3)	0.054 (2)	0.079 (2)	−0.018 (2)	−0.014 (2)	0.0031 (17)
C16	0.0524 (18)	0.082 (2)	0.0536 (19)	−0.0020 (19)	−0.0015 (16)	0.0041 (17)
C17	0.129 (4)	0.126 (4)	0.077 (3)	−0.042 (4)	0.018 (3)	0.021 (3)
C18	0.077 (2)	0.130 (3)	0.057 (2)	0.019 (3)	−0.017 (2)	−0.009 (2)
C19	0.129 (4)	0.091 (3)	0.087 (3)	0.044 (3)	0.007 (3)	−0.018 (2)
O1	0.0360 (11)	0.143 (2)	0.0685 (15)	0.0035 (15)	0.0004 (12)	0.0002 (15)
O2	0.0438 (11)	0.0629 (13)	0.0623 (13)	−0.0109 (12)	−0.0077 (11)	−0.0014 (11)

C1—C10	1.514 (4)	C11—H11B	0.9700
C1—C14	1.552 (5)	C12—C13	1.495 (6)
C1—C2	1.571 (4)	C12—H12A	0.9700
C1—H1	0.9800	C12—H12B	0.9700
C2—C7	1.538 (4)	C13—C14	1.536 (5)
C2—C15	1.541 (4)	C13—H13A	0.9700
C2—C3	1.542 (4)	C13—H13B	0.9700
C3—O2	1.427 (3)	C14—C19	1.535 (5)
C3—C4	1.486 (4)	C14—H14	0.9800
C3—H3	0.9800	C15—H15A	0.9600
C4—C5	1.330 (4)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.485 (4)	C16—C18	1.511 (5)
C5—C16	1.501 (4)	C16—C17	1.515 (5)
C6—O1	1.224 (4)	C16—H16	0.9800
C6—C7	1.512 (5)	C17—H17A	0.9600
C7—C8	1.522 (4)	C17—H17B	0.9600
C7—H7	0.9800	C17—H17C	0.9600
C8—C9	1.478 (4)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C9—C10	1.317 (4)	C19—H19A	0.9600
C9—H9	0.9300	C19—H19B	0.9600
C10—C11	1.496 (5)	C19—H19C	0.9600
C11—C12	1.505 (6)	O2—H2o	0.8200
C11—H11A	0.9700
C10—C1—C14	110.3 (3)	H11A—C11—H11B	107.9
C10—C1—C2	113.7 (2)	C13—C12—C11	109.6 (4)
C14—C1—C2	115.8 (3)	C13—C12—H12A	109.7
C10—C1—H1	105.3	C11—C12—H12A	109.7
C14—C1—H1	105.3	C13—C12—H12B	109.7
C2—C1—H1	105.3	C11—C12—H12B	109.7
C7—C2—C15	106.6 (3)	H12A—C12—H12B	108.2
C7—C2—C3	108.0 (2)	C12—C13—C14	114.1 (3)
C15—C2—C3	108.3 (2)	C12—C13—H13A	108.7
C7—C2—C1	111.3 (2)	C14—C13—H13A	108.7
C15—C2—C1	109.4 (2)	C12—C13—H13B	108.7
C3—C2—C1	113.0 (2)	C14—C13—H13B	108.7
O2—C3—C4	109.3 (2)	H13A—C13—H13B	107.6
O2—C3—C2	110.2 (2)	C19—C14—C13	106.9 (3)
C4—C3—C2	112.8 (2)	C19—C14—C1	115.2 (4)
O2—C3—H3	108.1	C13—C14—C1	111.5 (3)
C4—C3—H3	108.1	C19—C14—H14	107.6
C2—C3—H3	108.1	C13—C14—H14	107.6
C5—C4—C3	126.5 (3)	C1—C14—H14	107.6
C5—C4—H4	116.8	C2—C15—H15A	109.5
C3—C4—H4	116.8	C2—C15—H15B	109.5
C4—C5—C6	117.5 (3)	H15A—C15—H15B	109.5
C4—C5—C16	125.5 (3)	C2—C15—H15C	109.5
C6—C5—C16	117.0 (3)	H15A—C15—H15C	109.5
O1—C6—C5	120.6 (3)	H15B—C15—H15C	109.5
O1—C6—C7	120.0 (3)	C5—C16—C18	113.0 (3)
C5—C6—C7	119.2 (3)	C5—C16—C17	109.8 (3)
C6—C7—C8	107.5 (3)	C18—C16—C17	110.9 (3)
C6—C7—C2	113.6 (2)	C5—C16—H16	107.6
C8—C7—C2	114.4 (3)	C18—C16—H16	107.6
C6—C7—H7	107.0	C17—C16—H16	107.6
C8—C7—H7	107.0	C16—C17—H17A	109.5
C2—C7—H7	107.0	C16—C17—H17B	109.5
C9—C8—C7	109.8 (3)	H17A—C17—H17B	109.5
C9—C8—H8A	109.7	C16—C17—H17C	109.5
C7—C8—H8A	109.7	H17A—C17—H17C	109.5
C9—C8—H8B	109.7	H17B—C17—H17C	109.5
C7—C8—H8B	109.7	C16—C18—H18A	109.5
H8A—C8—H8B	108.2	C16—C18—H18B	109.5
C10—C9—C8	124.9 (3)	H18A—C18—H18B	109.5
C10—C9—H9	117.6	C16—C18—H18C	109.5
C8—C9—H9	117.6	H18A—C18—H18C	109.5
C9—C10—C11	120.5 (3)	H18B—C18—H18C	109.5
C9—C10—C1	124.1 (3)	C14—C19—H19A	109.5
C11—C10—C1	115.2 (3)	C14—C19—H19B	109.5
C10—C11—C12	112.2 (4)	H19A—C19—H19B	109.5
C10—C11—H11A	109.2	C14—C19—H19C	109.5
C12—C11—H11A	109.2	H19A—C19—H19C	109.5
C10—C11—H11B	109.2	H19B—C19—H19C	109.5
C12—C11—H11B	109.2	C3—O2—H2o	109.5
C10—C1—C2—C7	−26.9 (3)	C15—C2—C7—C8	171.6 (3)
C14—C1—C2—C7	−156.1 (3)	C3—C2—C7—C8	−72.2 (3)
C10—C1—C2—C15	−144.5 (3)	C1—C2—C7—C8	52.4 (3)
C14—C1—C2—C15	86.3 (4)	C6—C7—C8—C9	−176.9 (3)
C10—C1—C2—C3	94.8 (3)	C2—C7—C8—C9	−49.8 (4)
C14—C1—C2—C3	−34.5 (4)	C7—C8—C9—C10	23.6 (5)
C7—C2—C3—O2	74.3 (3)	C8—C9—C10—C11	−176.3 (3)
C15—C2—C3—O2	−170.6 (3)	C8—C9—C10—C1	0.0 (6)
C1—C2—C3—O2	−49.2 (3)	C14—C1—C10—C9	133.7 (4)
C7—C2—C3—C4	−48.2 (3)	C2—C1—C10—C9	1.7 (5)
C15—C2—C3—C4	67.0 (3)	C14—C1—C10—C11	−49.8 (4)
C1—C2—C3—C4	−171.7 (3)	C2—C1—C10—C11	178.2 (3)
O2—C3—C4—C5	−99.1 (4)	C9—C10—C11—C12	−128.9 (4)
C2—C3—C4—C5	23.9 (4)	C1—C10—C11—C12	54.5 (5)
C3—C4—C5—C6	0.8 (5)	C10—C11—C12—C13	−55.1 (5)
C3—C4—C5—C16	−179.5 (3)	C11—C12—C13—C14	55.9 (5)
C4—C5—C6—O1	176.7 (3)	C12—C13—C14—C19	−179.9 (4)
C16—C5—C6—O1	−3.1 (5)	C12—C13—C14—C1	−53.1 (5)
C4—C5—C6—C7	2.3 (4)	C10—C1—C14—C19	169.7 (3)
C16—C5—C6—C7	−177.4 (3)	C2—C1—C14—C19	−59.4 (4)
O1—C6—C7—C8	−77.0 (4)	C10—C1—C14—C13	47.6 (4)
C5—C6—C7—C8	97.4 (3)	C2—C1—C14—C13	178.5 (3)
O1—C6—C7—C2	155.4 (3)	C4—C5—C16—C18	−18.6 (5)
C5—C6—C7—C2	−30.2 (4)	C6—C5—C16—C18	161.2 (3)
C15—C2—C7—C6	−64.5 (3)	C4—C5—C16—C17	105.8 (4)
C3—C2—C7—C6	51.7 (3)	C6—C5—C16—C17	−74.5 (4)
C1—C2—C7—C6	176.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1i	0.82	2.02	2.804 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯O1i	0.82	2.02	2.804 (3)	160

Symmetry code: (i) .